Departmental Seminar
Semester 1, 2015
Department of Chemistry & Biomolecular Sciences
Macquarie University, Sydney Australia
The Speaker
Professor Marisa C. Kozlowski
Department of Chemistry
University of Pennsylvania
Fellow of the American Chemical Society
Fellow of American Association for the Advancement of Science
Adventures in Oxidative Bond Forming Reactions: Development
and Applications in Natural Product Synthesis
Apri 20th Monday 1 pm
F7B 322 (CBMS Tea Room)
About the Speaker
Marisa Kozlowski earned an A.B. from Cornell University in 1989 and a Ph.D. from the University of
California at Berkeley in 1994. After a National Science Foundation postdoctoral fellowship with David A. Evans
at Harvard University, she joined the faculty at the University of Pennsylvania where she currently holds the rank
of Professor of Chemistry. In addition to over 100 independent publications, Professor Kozlowski coauthored the
book “Fundamentals of Asymmetric Catalysis". She is currently the 2015 National Organic Symposium Organizer,
a member of the Organic Reactions Editorial Board, and an Associate Editor for the Journal of Organic Chemistry.
Synopsis
Inspired by Nature's use of oxidative couplings to construct C–C, C–O, C–N bonds in many natural products,
we have undertaken studies of these important transformations. The development of selective catalytic processes
for naphthol coupling, phenol coupling, and N-arylation that utilize oxygen as the terminal oxidant will be
discussed. Applications to the synthesis of chiral natural products including nigerone, hypocrellin, cercosporin,
and bisoranjidiol as well as to the synthesis of novel optically active materials will be presented.
Representative Publications
“Vanadium-Catalyzed Regioselective Oxidative Coupling of 2-Hydroxycarbazoles” Org. Lett. 2015, ASAP
“Recent Advances in Asymmetric Catalytic Methods for the Formation of Acyclic alpha, alpha-Disubstituted
alpha-Amino Acids” J. Org. Chem. 2015, 80, 1–7.
“Chemoselective Activation of sp3 vs sp3 C–H Bonds with Pd(II)” J. Am. Chem. Soc. 2015, 137, 18–21.
“Cinchonidinium Acetate as a Convenient Catalyst for the Asymmetric Synthesis of Unsymmetric cisStilbenediamines”Tetrahedron Lett. 2015, In Press.
“Selective Oxidative Homo- and Cross-Coupling of Phenols with Aerobic Catalysts” J. Am. Chem. Soc. 2014, 136,
6782-6785.
“Axial Chiral Bisbenzophenazines: Solid-State Self-Assembly via Halide Hydrogen Bonds Triggered by Linear
Alkanes” J. Am. Chem. Soc. 2014, 136, 10601–10604.
“Perylenequinones: Isolation, Synthesis and Biological Activity” Eur. J. Org. Chem. 2012, 21, 3887-3094.
“Enantioselective Total Synthesis of (S)-Bisoranjidiol, an Axially Chiral Bisanthraquinone” Org. Lett. 2012, 14,
1408–1411.